25 American Towns Where People Live Like They're in Europe

23. Jacksonville, Oregon: A Tuscan Hill Town with a Western Twist

With its golden hills, vineyard-draped landscapes, and sun-soaked stone buildings, Jacksonville, Oregon, feels like a slice of the Tuscan countryside dropped into the American West. Originally a booming gold rush town, it now thrives as a hub for wine lovers and culture seekers. The town’s historic district is a blend of preserved frontier architecture and Mediterranean warmth—cobbled sidewalks, rustic facades, and terracotta-tinted buildings surrounded by cypress trees and vineyards. It’s the gateway to the Applegate Valley Wine Trail, where boutique wineries and olive groves channel the feel of a relaxed Italian getaway. The local farmers’ markets, outdoor concerts, and world-renowned Britt Music Festival add a cultural layer that brings the whole town to life. Whether you're sipping a glass of pinot noir under the Oregon sun or exploring artisan shops in historic storefronts, Jacksonville combines the charm of Tuscany with the heart of the American frontier.